Insecticidal use of fluoroacetamide



Patented May 3, 1949 UNITED STATES Nellie M. O. Payne, Stamford, COHIL, assignor to TENT GFFICE American Cyanamid Company,

New York,

N. Y., a corporation of Maine No Drawing. Application May 24, 1944, Serial No. 537,185

1 Claim.

The present invention relates to the use of organic fluorine compounds which are innocuous to plants as insecticides.

The invention is specifically concerned the use of those aliphatic fluorine compounds where the fluorine is attached to a carbon atom which is itself directly attached to a carbonyl group, the pH of the compounds being not less than 4.0. These compounds may be esters, amides, ketones or aldehydes, and will be found to be effective insecticides so long as the above specified. fluorine relationship is maintained, so long as there is no other halogen attached to the alpha carbon atom, and will produce no plant injury so long as ones are used having a pH no less than 4-.0.

These compounds will be found to have insecticidal toxicity not only when used as contact materials and as stomach poisons and synergists, but those materials capable of being readily vaporized will be found to be excellent fumigants.

By a pH not less than 4.0 is meant that pH measurement in water as a one-hundredth molar solution. It has been found if such compounds having a pH below 4.0 are used, a definite plant injury occurs. Perhaps fiuoroacetic acid is most typical of those compounds which will burn or otherwise injure foliage and hence are not contemplated by the present invention. Fluoroacetic acid as a one-hundredth molar solution in water has a pH of 2.3. Tests have demonstrated that so long as the pH under the above conditions is greater than 4.0 such solutions are innocuous to plant life yet toxic to insects. This is a fortuitous circumstance as all compounds of the present group except the acid have a pi-l under the above conditions of 4.0 or above.

As showing the unexpected effect of such compounds using fiuoroacetamide as an example and as compared with other compounds having either an acetarnide group or other halogen or substituents attached to the acetamide group, tests were made on Aphlis rumicis L. on nasturtiums in a water solution as a spray. As little as 6.8 parts per million of fiuoroacetamide were found to give effective kills on these insects, while no plant injury occured.

On the contrary, where chlorine was substituted for the fluorine, 34 parts per million of chloroacetamide were required to give the same kill. Thiocyanoacetamide required 620 parts per million for the same toxicity.

It was thought that by introducing two chlorine atoms in addition to the fluorine in an acetamide molecule, the toxicity could be stepped up but upon actual tests on these insects, it required 14,000 parts per million of dichlorofluoroacetamide to give the same kill as 6.8 parts per million of fiuoroacetamide.

The above results point clearly to the uniqueness of these compounds as insecticides.

A further series of experiments were conducted on Aphis rumicz's L., also on nasturtiums, using a large number of related materials. In all cases, a water solution of the compounds was used containing the wetting agent commercially known as Vatsol O. T. (dioctyl sodium sulfosuccinate) in the ratio of 1 to 5000, with the following results:

For instance, a .2% water solution of fluoroacetarnide gave kill, whereas the same concentration of acetamide killed only 11.2%; chloroacetamide killed 81%; thiocyanoacetamide killed 74.4%; dibromacetamide gave an 85.3% kill, while there was no kill whatever with cyanoacetamide or dichlorofiuoroacetamide.

On further dilution, the other compounds which had shown some kill dropped off rapidly to zero while fiuoroacetamide at even as low as .00312%, which is one part in thirty-two thousand, still gave a kill of 89%, and at a dilution of .00156%, which is one part in sixty-four thousand, still gave a kill of 75.8%.

Sodium fluoride is the standard stomach poison for Trzbolium confusum (adults). When this material was fed to these insects in a 2% mix in flour it gave a 17.6% kill, while the same concentration of fluoroacetamide had a toxicity of 99.4%. When the sodium fluoride concentration was dropped to 1%, the kill was lowered to 5.7%. Even at this concentration, fluoroacetamide gave a 97.6% kill. Straight acetamide gave no kill whatever on these insects at either 1 or 2%.

In an attempt to determine whether the larvae of Tribolium confusum would succumb to fluoroacetamide, a spray was made of 1% fiuoroacetamide in water. As a result of this test, it was found that 80.6% of the larvae sprayed died. This figure represents the actual kill, even when corrected for the normal death rate during the test period.

A water solution of fluoroacetamide in a dilution of 1 to 500 with a wetting agent (Vatsol 0. T3) in a ratio of 1 to 5000, was sprayed on cockroaches with nearly a 100% kill.

Bean leaves, on which southern army worm larvae (Xylonyges eridana Cramer) were feeding, were sprayed with a water solution of fluoroacetamide at a dilution of 1 to 200. A 100% control of the larvae was obtained with the fluoroacetamide solution whereas sodium fluoride at the same dilution produced no kill. No injury to the leaves or plants resulted.

The California red scale (Aom'diella aurantii Mask.) was sprayed with a water solution of fiuoroacetamide containing the wetting agent, dioctyl sodium sulfosuccinate, in the ratio of 1 to 5000." A925 %-control Wasmbtained at a dilution of Mb 400.,

A water solution of fiuoroacetamide at a dilution of 1 to 200 used as a spray on Mexican bean beetle adults (Epilachna corrupta Muls.) gave a 100% kill. Sodium fiuoride'at-the same dilution gave only a 50% control.

A 0.1% water solution of;fluoromethyl. lauryl ketone containing the wetting agent, 0. T., in the ratio of 1 to 5000 was sprayed on black bean aphids growing on nasturtiumsri rNo plant injury occurred and a 95.8% control of the aphids was obtained.

Using ethyl fluoroacetate as a fumigant in a dosage ratio;of.-10, milligrarnsrper literior 1 hour, 100.%--= was ,obtained ont Tr z'bolium -conjusum (adults), .S'itophilus oryzae ,(adults) and Attagenus piceus (larvae).

This is a moSta-maZin'gLfumigant effect, for at this; dosage with these ;-ir-1se :,ts, ethylfiuoroacetate is-more toxic than hydrocyanic acid, which has been considered the. standard for a large number oi years.

A. water solution, o'f..lauryl fiuoroacetate at a dilution of -11 t0.2500:;used.as a sprayon California red scale (Aonidiellir aurantzi. Mask.) gave more than twice the kill obtained with lauryl chloroacetate at theisamadilution.

VA 90% control. of-,-black bean aphids feeeding on nasturtium plant's wasobtained with a 0.1% water solutionof calcium fiuoroacetate, without plant injury. g

showingthe.synergistic. efiect of the com pounds of this; invention :withdioctyl fumarate, it. .was .found. that with aifsolutionn containing -.025%. oftoxicmater'ial in .water and consisting Vatsol of 95% dioctyl fumarate and 5% of lauryl fluoroacetate, the combination was 3.7 times as efiective against Aphis rumz'cz's L. as was the same concentration of dioctyl fumarate alone.

The compounds of this invention may therefore be used either alone or with other insecticides orzfumigants. v A number of experiments wereperformed to determine plant injury after having been sprayed "with water solutions of compounds of the present invention. Even at concentrations of 1 to 500, no injury was apparent to sweet peas, tomatoes, beans (London horticultural) and nasturtiums.

' These plants are very sensitive to injury when sprayed with insecticides and consequently, a material non-injurious thereto, can be considered as completely innocuous to the usual prises contacting them with a toxic amount of fiuoroacetamide.

NELLIE M. C. PAYNE.

REFERENCES CITED The vfollowing references are. of record in .the file of this patent:

UNITED STATES PATENTS Number Name Date 2,290,881 Katzman July 28, 1942 2,238,791 Weedon Jan. 11', 1944 

